Acetone → HCID 18323177, compound

HRID 613767Notes

Reaction equation

HRID 613767 reaction equation
[CH3:1][S:2][C:3]1[NH:4][C:5](=[O:15])[C:6]([CH3:14])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.CC(C)=O.CC(C)([O-])C.[K+].[C:26]1([S:32]Cl)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.O>[C:8]1([C:6]2([CH3:14])[C:5](=[O:15])[N:4]([S:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:3]([S:2][CH3:1])=[N:7]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 11008040Benzenesulfenyl chlorideHCID 183231654‐Methyl‐2‐(methylsulfanyl)‐4‐phenyl‐4,5‐dihydro‐ 1H‐imidazol‐5‐oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 18323177HCID 18323177, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.6 g (2.7 mmol) of 2-methylthio-4-methyl-4-phenyl-2-imidazolin-5-one in solution in 50 ml of anhydrous tetrahydrofuran (THF) is charged to a 100 ml, three-necked, round-bottomed flask under an inert atomsphere. The solution is stirred with a magnetic stirrer and is cooled to 0° C. (ice bath+acetone). 0.30 g (1 molar equivalent) of potassium tert-butoxide is added and the mixture is stirred for 10 minutes at 0° C. A solution containing 0.40 g of phenylsulfenyl chloride (phenylthio chloride) and 10 ml of anhydrous THF is then run in. The mixture is then left to return to room temperature for one hour. The reaction mixture is run into 100 ml of water. Extraction is carried out with 100 ml of ethyl acetate. The organic phase is washed 4 times wtih water and dried over sodium sulfate.

Workup

  1. stirringthe mixture is stirred for 10 minutes at 0° C
  2. waitThe mixture is then left
  3. extractionExtraction
  4. washThe organic phase is washed 4 times wtih water
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-a050b9959bab4ef2b933847e23a6890e
Source dataset
uspto-grants-1999_12
Patent number
US06008370

Reaction notes

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